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  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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  • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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  • C09K19/3001—Cyclohexane rings
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  • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B30/00—Optical systems or apparatus for producing three-dimensional [3D] effects, e.g. stereoscopic images
  • G02B30/20—Optical systems or apparatus for producing three-dimensional [3D] effects, e.g. stereoscopic images by providing first and second parallax images to an observer's left and right eyes
  • G02B30/22—Optical systems or apparatus for producing three-dimensional [3D] effects, e.g. stereoscopic images by providing first and second parallax images to an observer's left and right eyes of the stereoscopic type
  • G02B30/24—Optical systems or apparatus for producing three-dimensional [3D] effects, e.g. stereoscopic images by providing first and second parallax images to an observer's left and right eyes of the stereoscopic type involving temporal multiplexing, e.g. using sequentially activated left and right shutters
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  • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
  • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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  • C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
  • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
  • C09K2019/122—Ph-Ph
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  • C09K19/3001—Cyclohexane rings
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  • C09K19/3001—Cyclohexane rings
  • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
  • C09K2019/3007—Cy-Cy-Cy-Cy or more Cy rings
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  • C09K19/3001—Cyclohexane rings
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  • C09K2019/3025—Cy-Ph-Ph-Ph
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  • C09K2219/15—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used used as a medium, in which chemical reactions take place
• • G—PHYSICS
  • G02—OPTICS
  • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
  • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
  • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
  • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
  • G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
• • G—PHYSICS
  • G02—OPTICS
  • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
  • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
  • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
  • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
  • G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
  • G02F1/13706—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering the liquid crystal having positive dielectric anisotropy

Definitions

• the present invention relates to LC (LC) media and to LC displays (LCDs) containing these media, especially to LCDs addressed by an active matrix and in particular to LCDs of the IPS, PS-IPS, FFS, PS-FFS, HB-FFS, U-IPS, TN, PS-TN, STN or TN-TFT mode.
• LC LC
• LCDs LC displays
• LCDs are used in many areas for the display of information. LCDs are used both for direct-view displays and for projection-type displays.
• the electro-optical modes used are, for example, the t wisted n ematic (TN), s uper t wisted n ematic (STN), o ptically c ompensated b end (OCB) and e lectrically c ontrolled b irefringence (ECB) modes together with their various modifications, as well as others. All these modes utilise an electric field which is substantially perpendicular to the substrates or the LC layer.
• electro-optical modes that utilise an electric field which is substantially parallel to the substrates or the LC layer, such as, for example, the i n- p lane s witching (IPS) mode (as disclosed, for example, in DE 40 00 451 and EP 0 588 568 ) and the f ringe f ield s witching (FFS) mode, in which a strong "fringe field" is present, i.e. a strong electric field close to the edge of the electrodes and, throughout the cell, an electric field which has both a strong vertical component and a strong horizontal component.
• IPS i n- p lane s witching
• FFS f ringe f ield s witching
• liquid crystals according to the present invention are preferably used in displays of this type.
• dielectrically positive LC media having rather lower values of the dielectric anisotropy are used in FFS displays, but in some cases LC media having a dielectric anisotropy of only about 3 or even less are also used in IPS displays.
• PS polymer sustained
• PSA polymer sustained alignment
• a small amount for example 0.3% by weight, typically ⁇ 1% by weight
• the polymerisation is carried out at a temperature where the LC medium exhibits an LC phase, usually at room temperature.
• RMs reactive mesogens
• LC media having improved properties are required.
• the addressing times in particular have to be improved for many types of application.
• LC media having lower viscosities ( ⁇ ), especially having lower rotational viscosities ( ⁇ 1 ) are required.
• the media must have a nematic phase range of suitable width and position and an appropriate birefringence ( ⁇ n), and the dielectric anisotropy ( ⁇ ) should be sufficiently high to allow a reasonably low operating voltage.
• the displays according to the present invention are preferably addressed by an active matrix (a ctive m atrix LC D s, AMDs for short), preferably by a matrix of t hin f ilm t ransistors (TFTs).
• active matrix a ctive m atrix LC D s, AMDs for short
• TFTs matrix of t hin f ilm t ransistors
• the liquid crystals according to the invention can also advantageously be used in displays having other known addressing means.
• LC media which are suitable for LCDs and especially for IPS displays are known, for example, from JP 07-181 439 (A ), EP 0 667 555 , EP 0 673 986 , DE 195 09 410 , DE 195 28 106 , DE 195 28 107 , WO 96/23 851 and WO 96/28 521 .
• these LC media have certain disadvantages. Amongst other deficiencies, most of them result in disadvantageously long addressing times, have inadequate values of the resistivity and/or require excessively high operating voltages. Both an improvement in the operating properties and also in the shelf life are necessary here.
• LC media for use in the expanding market of public information displays (PIDs) and automotive displays a high reliability and a wide operating range are highly important factors.
• LC media with high clearing temperature (Tni), good LTS (Low Temperature Stability) and high reliability are therefore desired.
• the invention has the object of providing media, in particular for FFS, IPS, TN or STN displays of this type, in particular for active matrix displays like those of the TFT (thin film transistor) type, which do not exhibit the disadvantages indicated above or only do so to a lesser extent and preferably exhibit one or more of a wide operating range, a high clearing temperature, a high reliability, a low threshold voltage, a high dielectric anisotropy, a good low temperature stability (LTS), a low rotational viscosity and fast response times.
• TFT thin film transistor
• the invention relates to an LC medium with positive dielectric anisotropy, characterised in that it contains one or more compounds of formula I in a concentration of >0 and ⁇ 10% in which R 1 and R 2 independently of each other denote alkyl having 1 to 6 C atoms.
• the LC medium has a birefringence ⁇ 0.15, more preferably from 0.8 to 0.15.
• the invention further relates to the use of an LC medium as described above and below for electro-optical purposes, in particular for the use in shutter glasses, for 3D applications, in IPS, PS-IPS, FFS, PS-FFS, HB-FFS, U-IPS, TN, PS-TN, STN or TN-TFT displays.
• the invention further relates to an electro-optical LC display containing an LC medium as described above and below, in particular an IPS, PS-IPS, FFS, PS-FFS, HB-FFS, U-IPS, TN, PS-TN, STN or TN-TFT display.
• an IPS, PS-IPS, FFS, PS-FFS, HB-FFS, U-IPS, TN, PS-TN, STN or TN-TFT display in particular an IPS, PS-IPS, FFS, PS-FFS, HB-FFS, U-IPS, TN, PS-TN, STN or TN-TFT display.
• the invention furthermore relates to a process for preparing an LC medium as described above and below, comprising the steps of mixing one or more compounds of formula I with one or more further LC compounds and optionally one or more additives.
• all atoms also include their isotopes.
• one or more hydrogen atoms (H) may be replaced by deuterium (D), which is particularly preferred in some embodiments; a high degree of deuteration enables or simplifies analytical determination of compounds, in particular in the case of low concentrations.
• R 0 denotes an alkyl radical and/or an alkoxy radical, this may be straight-chain or branched. It is preferably straight-chain, has 2, 3, 4, 5, 6 or 7 C atoms and accordingly preferably denotes ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy or heptyloxy, furthermore methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.
• R 0 preferably denotes straight-chain alkyl having 2-6 C atoms.
• R 0 denotes an alkyl or alkenyl radical which is at least monosubstituted by halogen
• this radical is preferably straight-chain, and halogen is preferably F or Cl.
• halogen is preferably F.
• the resultant radicals also include perfluorinated radicals.
• the fluorine or chlorine substituent may be in any desired position, but is preferably in the ⁇ -position.
• X 0 is preferably F, Cl or a mono- or polyfluorinated alkyl or alkoxy radical having 1, 2 or 3 C atoms or a mono- or polyfluorinated alkenyl radical having 2 or 3 C atoms.
• X 0 denotes F or OCF 3 , preferably F.
• R 1 and R 2 are preferably selected from ethyl, propyl, butyl and pentyl, all of which are straight-chain.
• Preferred compounds of the formula I are selected from the following subformulae.
• the concentration of the compounds of formula I and its subformulae in the LC medium is preferably from 0.2 to 10%, more preferably from 1.0 to 10%, very preferably from 1.0 to 8%.
• the LC medium contains 1, 2 or 3 compounds of formula I or its subformulae.
• LC media are selected from the following preferred embodiments, including any combination thereof:
• alkyl or "alkyl*" in this application encompasses straight-chain and branched alkyl groups having 1-6 carbon atoms, in particular the straight-chain groups methyl, ethyl, propyl, butyl, pentyl and hexyl. Groups having 2-5 carbon atoms are generally preferred.
• alkenyl or “alkenyl*” encompasses straight-chain and branched alkenyl groups having 2-6 carbon atoms, in particular the straight-chain groups.
• Preferred alkenyl groups are C 2 -C 7 -1 E-alkenyl, C 4 -C 6 -3E-alkenyl, in particular C 2 -C 6 -1 E-alkenyl.
• alkenyl groups are vinyl, 1E-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 4-pentenyl, 4Z-hexenyl, 4E-hexenyl and 5-hexenyl.
• fluoroalkyl preferably encompasses straight-chain groups having a terminal fluorine, i.e. fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl and 7-fluoroheptyl.
• fluorine i.e. fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl and 7-fluoroheptyl.
• other positions of the fluorine are not excluded.
• R 0 and X 0 Through a suitable choice of the meanings of R 0 and X 0 , the addressing times, the threshold voltage, the steepness of the transmission characteristic lines, etc., can be modified in the desired manner.
• 1E-alkenyl radicals, 3E-alkenyl radicals, 2E-alkenyloxy radicals and the like generally result in shorter addressing times, improved nematic tendencies and a higher ratio between the elastic constants k 33 (bend) and k 11 (splay) compared with alkyl and alkoxy radicals.
• 4-Alkenyl radicals, 3-alkenyl radicals and the like generally give lower threshold voltages and lower values of k 33 /k 11 compared with alkyl and alkoxy radicals.
• the mixtures according to the invention are distinguished, in particular, by high ⁇ values and thus have significantly faster response times than the mixtures from the prior art.
• the optimum mixing ratio of the compounds of the above-mentioned formulae depends substantially on the desired properties, on the choice of the components of the above-mentioned formulae and on the choice of any further components that may be present.
• the total amount of compounds of the above-mentioned formulae in the LC media according to the invention is not crucial.
• the mixtures can therefore comprise one or more further components for the purposes of optimisation of various properties.
• the observed effect on the desired improvement in the properties of the medium is generally greater, the higher the total concentration of compounds of the above-mentioned formulae.
• the LC medium additionally comprises one or more polymerisable compounds.
• the polymerisable compounds are preferably selected from formula M R a -B 1 -(Z b -B 2 ) m -R b M in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
• Particularly preferred compounds of the formula I are those in which B 1 and B 2 each, independently of one another, denote 1,4-phenylene, 1,3-phenylene, naphthalene-1,4-diyl, naphthalene-2,6-diyl, phenanthrene-2,7-diyl, 9,10-dihydro-phenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7-diyl, coumarine, flavone, where, in addition, one or more CH groups in these groups may be replaced by N, cyclohexane-1,4-diyl, in which, in addition, one or more non-adjacent CH 2 groups may be replaced by O and/or S, 1,4-cyclohexenylene, bicycle[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl,
• Particularly preferred compounds of the formula M are those in which B 1 and B 2 each, independently of one another, denote 1,4-phenylene, 1,3-phenylene, naphthalene-1,4-diyl or naphthalene-2,6-diyl,
• Very preferred compounds of formula M are selected from the following formulae: in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
• trireactive compounds M15 to M31 in particular M17, M18, M19, M22, M23, M24, M25, M30, M31 and M32.
• the group is preferably wherein L on each occurrence, identically or differently, has one of the meanings given above or below, and is preferably F, Cl, CN, NO 2 , CH 3 , C 2 H 5 , C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 )C 2 H 5 , OCH 3 , OC 2 H 5 , COCH 3 , COC 2 H 5 , COOCH 3 , COOC 2 H 5 , CF 3 , OCF 3 , OCHF 2 , OC 2 F 5 or P-Sp-, very preferably F, Cl, CN, CH 3 , C 2 H 5 , OCH 3 , COCH 3 , OCF 3 or P-Sp-, more preferably F, Cl, CH 3 , OCH 3 , COCH 3 oder OCF 3 , especially F or CH 3 .
• Preferred compounds of formulae M1 to M32 are those wherein P 1 , P 2 and P 3 denote an acrylate, methacrylate, oxetane or epoxy group, very preferably an acrylate or methacrylate group.
• Further preferred compounds of formulae M1 to M32 are those wherein one of Sp 1 , Sp 2 and Sp 3 is a single bond and another one of Sp 1 , Sp 2 and Sp 3 is different from a single bond.
• Further preferred compounds of formulae M1 to M32 are those wherein those groups Sp 1 , Sp 2 and Sp 3 that are different from a single bond denote -(CH 2 ) s1 -X"-, wherein s1 is an integer from 1 to 6, preferably 2, 3, 4 or 5, and X" is X" is the linkage to the benzene ring and is -O-, -O-CO-, -CO-O-, -O-CO-O- or a single bond.
• polymerisable compounds of formulae M1 to M32 are those selected from Table D below.
• LC media comprising one, two or three polymerisable compounds of formula M, preferably selected from formulae M1 to M32.
• the proportion of polymerisable compounds, including those of formula M and its subformulae, in the LC medium is from 0.01 to 5%, very preferably from 0.05 to 1%, most preferably from 0.1 to 0.5%.
• Such an LC medium is especially suitable for use in PSA displays where it shows low image sticking, a quick and complete polymerisation, the quick generation of a low pretilt angle which is stable after UV exposure, a high reliability, high VHR value after UV exposure, and a high birefringence.
• the polymerisable compounds it is possible to increase the absorption of the LC medium at longer UV wavelengths, so that it is possible to use such longer UV wavelengths for polymerisation, which is advantageous for the display manufacturing process.
• the polymerisable group P is a group which is suitable for a polymerisation reaction, such as, for example, free-radical or ionic chain polymerisation, polyaddition or polycondensation, or for a polymer-analogous reaction, for example addition or condensation onto a main polymer chain.
• a polymerisation reaction such as, for example, free-radical or ionic chain polymerisation, polyaddition or polycondensation, or for a polymer-analogous reaction, for example addition or condensation onto a main polymer chain.
• groups which are suitable for polymerisation with ring opening such as, for example, oxetane or epoxide groups.
• polymerisable groups P are selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxide, most preferably from acrylate and methacrylate.
• Sp is different from a single bond, it is preferably of the formula Sp"-X", so that the respective radical P-Sp- conforms to the formula P-Sp"-X"-, wherein
• X" is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR 0 -CO-, -NR 0 -CO-NR 00 - or a single bond.
• Typical spacer groups Sp and -Sp"-X"- are, for example, -(CH 2 ) p1 -, - (CH 2 CH 2 O) q1 -CH 2 CH 2 -, -CH 2 CH 2 -S-CH 2 CH 2 -, -CH 2 CH 2 -NH-CH 2 CH 2 - or - (SiR 0 R 00 -O) p1 -, in which p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R 0 and R 00 have the meanings indicated above.
• Particularly preferred groups Sp and -Sp"-X"- are -(CH 2 ) p1 -, -(CH 2 ) p1 -O-, -(CH 2 ) p1 -O-CO-, -(CH 2 ) p1 -CO-O-, -(CH 2 ) p1 -O-CO-O-, in which p1 and q1 have the meanings indicated above.
• Particularly preferred groups Sp" are, in each case straight-chain, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methylimino-ethylene, 1-methylalkylene, ethenylene, propenylene and butenylene.
• the polymerisable compounds contained in the LC medium are polymerised or crosslinked (if one compound contains two or more polymerisable groups) by in-situ polymerisation in the LC medium between the substrates of the LC display, optionally while a voltage is applied to the electrodes.
• the structure of the PSA displays according to the invention corresponds to the usual geometry for PSA displays, as described in the prior art cited at the outset. Geometries without protrusions are preferred, in particular those in which, in addition, the electrode on the colour filter side is unstructured and only the electrode on the TFT side has slots. Particularly suitable and preferred electrode structures for PS-VA displays are described, for example, in US 2006/0066793 A1 .
• LC media containing polymerisable compounds allows the rapid establishment of a particularly low pretilt angle in PSA displays.
• the LC media exhibit significantly shortened response times, in particular also the grey-shade response times, in PSA displays compared with the media from the prior art.
• the invention also relates to the use of an LC medium according to the present invention as described above and below for electro-optical purposes, in particular for the use is in shutter glasses, for 3D applications, in IPS, PS-IPS, FFS, PS-FFS, HB-FFS, U-IPS, TN, PS-TN, STN or TN-TFT displays, and to electro-optical displays, in particular of the aforementioned types, containing an LC medium according to the present invention as described above and below, in particular an IPS, PS-IPS, FFS, PS-FFS, HB-FFS, U-IPS, TN, PS-TN, STN or TN-TFT display.
• the invention also relates to electro-optical displays, such as, for example, STN or MLC displays, having two plane-parallel outer plates, which, together with a frame, form a cell, integrated non-linear elements for switching individual pixels on the outer plates, and a nematic LC mixture having positive dielectric anisotropy and high specific resistance located in the cell, wherein the a nematic LC mixture is an LC medium according to the present invention as described above and below.
• electro-optical displays such as, for example, STN or MLC displays, having two plane-parallel outer plates, which, together with a frame, form a cell, integrated non-linear elements for switching individual pixels on the outer plates, and a nematic LC mixture having positive dielectric anisotropy and high specific resistance located in the cell, wherein the a nematic LC mixture is an LC medium according to the present invention as described above and below.
• the LC media according to the invention enable a significant broadening of the available parameter latitude.
• the achievable combinations of clearing point, viscosity at low temperature, thermal and UV stability and high optical anisotropy are far superior to previous materials from the prior art.
• the LC media according to the invention are suitable for mobile applications and TFT applications, such as, for example, mobile telephones and PDAs. Furthermore, the LC media according to the invention are particularly suitably for use in FFS and IPS displays.
• the LC media according to the invention preferably retain the nematic phase down to -20°C very preferably down to -30°C, most preferably down to -40°C.
• the LC media according to the invention preferably have a clearing point ⁇ 85°C, very preferably ⁇ 95°C, most preferably ⁇ 105°C.
• the LC media according to the invention preferably have a rotational viscosity ⁇ 1 of ⁇ 130 mPa ⁇ s, very preferably ⁇ 115 mPa ⁇ s, enabling excellent MLC displays having fast response times to be achieved.
• the rotational viscosities are determined at 20°C.
• the dielectric anisotropy ⁇ of the LC media according to the invention at 20°C is preferably ⁇ +4, very preferably ⁇ +6, most preferably ⁇ +8.
• the birefringence ⁇ n of the LC media according to the invention at 20°C is preferably in the range of from 0.080 to 0.150, more preferably from 0.090 to 0.140, particularly preferably 0.100 to 0.130.
• the nematic phase range of the LC media according to the invention preferably has a width of at least 100°, more preferably of at least 110 °C, in particular at least 130°. This range preferably extends at least from -25° to +105°C.
• the MLC displays according to the invention preferably operate at the first Gooch and Tarry transmission minimum [ C.H. Gooch and H.A. Tarry, Electron. Lett. 10, 2-4, 1974 ; C.H. Gooch and H.A. Tarry, Appl. Phys., Vol.
• the light stability and UV stability of the LC media according to the invention are considerably better, i.e. they exhibit a significantly smaller decrease in the HR on exposure to light, heat or UV.
• the construction of the MLC display according to the invention from polarisers, electrode base plates and surface-treated electrodes corresponds to the usual design for displays of this type.
• the term usual design is broadly drawn here and also encompasses all derivatives and modifications of the MLC display, in particular including matrix display elements based on poly-Si TFTs or MIM.
• the LC media which can be used in accordance with the invention are prepared in a manner conventional per se, for example by mixing one or more compounds of Claim 1 with one or more compounds of the formulae IV-XXX or with further LC compounds and/or additives.
• the desired amount of the components used in lesser amount is dissolved in the components making up the principal constituent, advantageously at elevated temperature. It is also possible to mix solutions of the components in an organic solvent, for example in acetone, chloroform or methanol, and to remove the solvent again, for example by distillation, after thorough mixing.
• the LC media may also comprise further additives known to the person skilled in the art and described in the literature, such as, for example, polymerisation initiators, inhibitors, surface-active substances, light stabilisers, antioxidants, e.g. BHT, TEMPOL, microparticles, free-radical scavengers, nanoparticles, etc.
• polymerisation initiators e.g. BHT, TEMPOL
• antioxidants e.g. BHT, TEMPOL
• microparticles e.g. BHT, TEMPOL
• microparticles e.g. ethylene glycol dimethoxys
• free-radical scavengers e.g., TEMPOL
• nanoparticles e.g., etc.
• 0-15% of pleochroic dyes or chiral dopants or initiators like Irgacure651® or Irgacure907® can be added.
• the LC media contain one or more chiral dopants, preferably in a concentration from 0.01 to 1% by weight, very preferably from 0.05 to 0.5% by weight.
• the chiral dopants are preferably selected from the group consisting of compounds from Table B below, very preferably from the group consisting of R- or S-1011, R- or S-2011, R- or S-3011, R- or S-4011, and R- or S-5011.
• the LC media contain a racemate of one or more chiral dopants, which are preferably selected from the chiral dopants mentioned in the previous paragraph.
• the LC media contain one or more further stabilisers, preferably selected from the the group consisting of the following formulae wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
• Preferred stabilisers of formula S3 are selected from formulaS3A wherein n2 is an integer from 1 to 12, and wherein one or more H atoms in the group (CH 2 ) n2 are optionally replaced by methyl, ethyl, propyl, butyl, pentyl or hexyl.
• Very preferred stabilisers are selected from the group consisting of the following formulae
• the LC medium comprises one or more stabilisers selected from the group consisting of formulae S1-1, S2-1, S3-1, S3-1 and S3-3.
• the LC medium comprises one or more stabilisers selected from Table D.
• the proportion of stabilisers, like those of formula S1-S3, in the LC medium is from 10 to 500 ppm,very preferably from 20 to 100 ppm.
• the LC medium according to the present invention contains a self-aligning (SA) additive, preferably in a concentration of 0.1 to 2.5 %.
• SA self-aligning
• Preferred SA additives for use in this preferred embodiment are selected from compounds comprising a mesogenic group and a straight-chain or branched alkyl side chain that is terminated with one or more polar anchor groups selected from hydroxy, carboxy, amino or thiol groups.
• SA additives contain one or more polymerisable groups which are attached, optionally via spacer groups, to the mesogenic group.
• These polymerisable SA additives can be polymerised in the LC medium under similar conditions as applied for the RMs in the PSA process.
• Suitable SA additives are disclosed for example in US 2013/0182202 A1 , US 2014/0838581 A1 , US 2015/0166890 A1 and US 2015/0252265 A1 .
• an LC medium or a polymer stabilised display according to the present invention contains one or more self-aligning additives selected from Table E below.
• the display according to the present invention does not contain an alignment layer.
• LC media for example, 0 to 15% by weight of pleochroic dyes, furthermore nanoparticles, conductive salts, preferably ethyldimethyldodecylammonium 4-hexoxybenzoate, tetrabutylammonium tetraphenylborate or complex salts of crown ethers (cf., for example, Haller et al., Mol. Cryst. Liq. Cryst. 24, 249-258 (1973 )), for improving the conductivity, or substances for modifying the dielectric anisotropy, the viscosity and/or the alignment of the nematic phases. Substances of this type are described, for example, in DE-A 22 09 127 , 22 40 864 , 23 21 632 , 23 38 281 , 24 50 088 , 26 37 430 and 28 53 728 .
• conductive salts preferably ethyldimethyldodecylammonium 4-hexoxybenz
• n and m each, independently of one another, denote 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, in particular 2, 3, 5, furthermore 0, 4, 6.
• LC media which, besides the compounds of the formula I, comprise at least one, two, three, four or more compounds from Table B.
• Table C Table C indicates possible dopants which are generally added to the LC media according to the invention.
• the LC media preferably comprise 0-10% by weight, in particular 0.01-5% by weight and particularly preferably 0.01-3% by weight of dopants.
• Table D Stabilisers which can additionally be added, for example, to the LC media according to the invention in amounts of 0-10% by weight, are mentioned below.
• Table E shows illustrative reactive mesogenic compounds (RMs) which can be used in the LC media in accordance with the present invention.
• the LC media according to the invention comprise one or more polymerisable compounds, preferably selected from the polymerisable compounds of the formulae RM-1 to RM-143.
• compounds RM-1, RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48, RM-52, RM-54, RM-57, RM-64, RM-74, RM-76, RM-88, RM-102, RM-103, RM-109, RM-117, RM-120, RM-121 and RM-122 are particularly preferred.
• Table E Table E shows self-alignment additives for vertical alignment which can be used in LC media according to the present invention together with the polymerizable compounds of formula I:
• the LC media and displays according to the present invention comprise one or more SA additives selected from formulae SA-1 to SA-48, preferably from formulae SA-14 to SA-48, very preferably from formulae SA-20 to SA-34 and SA-48, preferably in combination with one or more RMs of formula M.
• threshold voltage for the present invention relates to the capacitive threshold (V 0 ), also known as the Freedericks threshold, unless explicitly indicated otherwise.
• the optical threshold may also, as generally usual, be quoted for 10% relative contrast (V 10 ).
• the LC mixture C1 is formulated as follows: CDUQU-3-F 6.0% cl.p. 110.1°C DPGU-4-F 3.0% ⁇ n 0.1108 PGUQU-4-F 7.0% ⁇ +5.8 CCP-30CF3 8.0% ⁇ 8.9 CCP-40CF3 4.0% K 1 17.7 CCP-50CF3 3.0% K 3 18.7 CCP-V-1 18.0% K 3 /K 1 1.06 CCP-V2-1 9.0% V 0 1.84 V CLP-3-T 4.5% ⁇ 1 112 mPa ⁇ s PGP-2-2V 6.5% LTS -20°C 1000 h CC-3-V1 8.0% CCH-301 10.0% CCH-303 3.0% PCH-301 10.0%
• the LC mixture N1 is formulated as follows: CPGP-5-2 1.0% cl.p. 110.5°C CPGU-3-OT 1.5% ⁇ n 0.1105 CCG-V-F 8.5% ⁇ +5.8 CCP-3-1 5.0% ⁇ 8.9 CCP-3F.F.F 10.0% K 1 17.2 CCP-V-1 16.0% K 3 19.7 CCP-V2-1 9.0% K 3 /K 1 1.14 CCQU-2-F 5.0% V 0 1.82 V CCQU-3-F 10.0% CDU-2-F 10.0% LTS -20°C 1000 h PGP-2-2V 5.5% CC-3-V1 10.0% PP-1-2V1 7.0% PP-1-3 1.5%
• the mixture contains 1.0% of the compound CPGP-5-2 of formula I.
• the LC mixture N2 is formulated as follows: CPGP-5-2 1.0% cl.p. 109.7°C CPGU-3-OT 2.5% ⁇ n 0.1115 DGUQU-4-F 3.0% ⁇ +5.8 CCG-V-F 9.0% ⁇ 8.8 CCP-3-1 6.0% K 1 17.2 CCP-2F.F.F 5.0% K 3 19.4 CCP-3F.F.F 10.0% K 3 /K 1 1.13 CCP-5F.F.F 8.0% V 0 1.81 V CCP-V-1 16.0% CCP-V2-1 4.5% LTS -20°C 1000 h CCQU-3-F 10.0% PGP-2-2V 4.5% CC-3-V1 11.0% PP-1-2V1 4.5% PP-1-3 5.0%
• the mixture contains 1.0% of the compound CPGP-5-2 of formula I.
• VHR values of mixtures C11, N11 and N22 are measured at 100C, 3Hz and 1V in VHR test cell before and after light exposure using a LED lamp.
• the LC mixture C2 is formulated as follows: CPGU-3-OT 2.0% cl.p. 109.9°C DGUQU-4-F 2.5% ⁇ n 0.1116 CCG-V-F 11.0% ⁇ +5.6 CCP-3-1 5.0% ⁇ 8.6 CCP-3F.F.F 10.0% K 1 17.5 CCP-5F.F.F 8.0% K 3 19.2 CCP-V-1 12.0% K 3 /K 1 1.10 CCP-V2-1 6.0% V 0 1.85 V CCQU-2-F 5.0% CCQU-3-F 10.0% PGP-2-2V 8.0% CC-3-2V1 2.5% CC-3-V1 11.0% PP-1-2V1 2.5% PP-1-3 4.5%
• the mixture does not show satisfying LTS.
• the LC mixture N3 is formulated as follows: CPGP-5-2 0.5% cl.p. 110.0°C CPGU-3-OT 2.0% ⁇ n 0.1107 DGUQU-4-F 3.0% ⁇ +5.7 CCG-V-F 9.5% ⁇ 8.7 CCP-3-1 5.0% K 1 17.6 CCP-3F.F.F 10.0% K 3 19.2 CCP-5F.F.F 6.5% K 3 /K 1 1.09 CCP-V-1 14.0% V 0 CCP-V2-1 5.5% CCQU-2-F 6.0% CCQU-3-F 10.0% PGP-2-2V 6.5% CC-3-2V1 3.0% CC-3-V1 11.0% PP-1-2V1 2.5% PP-1-3 5.0%
• the mixture contains 0.5% of the compound CPGP-5-2 of formula I.
• the LC mixture N4 is formulated as follows: CPGP-5-2 1.0% cl.p. 109.4°C CPGU-3-OT 2.0% ⁇ n 0.1109 DGUQU-4-F 3.0% ⁇ +5.8 CCG-V-F 10.0% ⁇ 8.7 CCP-3-1 5.0% K 1 17.5 CCP-3F.F.F 10.0% K 3 19.4 CCP-5F.F.F 8.0% K 3 /K 1 1.11 CCP-V-1 12.5% V 0 1.83 V CCP-V2-1 5.5% LTS -20°C 1000 h CCQU-2-F 5.0% CCQU-3-F 10.0% PGP-2-2V 6.0% CC-3-2V1 3.0% CC-3-V1 11.0% PP-1-2V1 3.0% PP-1-3 5.0%
• the mixture contains 1.0% of the compound CPGP-5-2 of formula I, and shows good LTS at -20°C.
• the LC mixture N5 is formulated as follows: CPGP-5-2 2.0% cl.p. 109.3°C CPGU-3-OT 1.5% ⁇ n 0.1104 DGUQU-4-F 3.0% ⁇ +5.7 CCG-V-F 9.5% ⁇ 8.7 CCP-3-1 5.0% K 1 17.5 CCP-3F.F.F 10.0% K 3 19.3 CCP-5F.F.F 7.5% K 3 /K 1 1.10 CCP-V-1 14.0% V 0 1.84 V CCP-V2-1 4.0% LTS -20°C 1000 h CCQU-2-F 6.0% CCQU-3-F 10.0% PGP-2-2V 5.0% CC-3-2V1 3.0% CC-3-V1 11.0% PP-1-2V1 3.5% PP-1-3 5.0%
• the mixture contains 2.0% of the compound CPGP-5-2 of formula I, and shows good LTS at -20°C.
• the LC mixture N6 is formulated as follows: CPGP-5-2 4.0% cl.p. 109.3°C CPGU-3-OT 1.5% ⁇ n 0.1100 DGUQU-4-F 3.0% ⁇ +5.7 CCG-V-F 9.5% ⁇ 8.7 CCP-3-1 5.0% K 1 17.5 CCP-3F.F.F 10.0% K 3 19.6 CCP-5F.F.F 8.0% K 3 /K 1 1.12 CCP-V-1 14.0% V 0 1.83 V CCP-V2-1 2.5% LTS -20°C 1000 h CCQU-2-F 6.0% LTS -30°C 1000 h CCQU-3-F 10.0% PGP-2-2V 2.5% CC-3-2V1 3.0% CC-3-V1 11.0% PP-1-2V1 5.0% PP-1-3 5.0%
• the mixture contains 4.0% of the compound CPGP-5-2 of formula I, and shows good LTS at -20°C and -30°C.
• the LC mixture N7 is formulated as follows: CPGP-5-2 6.0% cl.p. 110.0°C CPGU-3-OT 1.5% ⁇ n 0.1094 DGUQU-4-F 2.0% ⁇ +5.8 CCG-V-F 10.0% ⁇ 8.8 CCP-3-1 4.5% K 1 17.5 CCP-3F.F.F 10.0% K 3 19.6 CCP-5F.F.F 9.5% K 3 /K 1 1.12 CCP-V-1 6.0% V 0 1.83 V CCP-V2-1 6.5% LTS -20°C 1000 h CCQU-2-F 8.0% LTS -30°C 1000 h CCQU-3-F 10.0% LTS -40°C 1000 h PGP-2-2V 1.5% CC-3-2V1 4.0% CC-3-V1 10.5% PP-1-2V1 5.0% PP-1-3 5.0%
• the mixture contains 6.0% of the compound CPGP-5-2 of formula I, and shows good LTS at -20°C, -30°C and -40°C.
• VHR values of mixtures C2, N4, N5, N6 and N7 are measured at at 60C, 60Hz/3Hz and 1V in VHR test cell before and after light exposure for varying using a LED lamp.
• Table 2 VHR values before and after BL load, 60Hz/60°C C2 N4 N5 N6 N7 VHR / % Initial 99.2 99.1 99.3 99.3 99.4 After BL 24h 93.8 94.0 94.1 94.3 94.5 After BL 120h 76.7 76.6 76.7 77.5 78.8
• Table 3 - VHR values before and after BL load, 3Hz/60°C C2 N4 N5 N6 N7 VHR / % Initial 93.0 93.6 94.5 94.4 94.8
• BL 24h 70.7 71.0 72.3 73.6 74.8 After BL 120h 21.6 21.7 22.0 23.0 24.5
• Example 7 To 99.65% of the LC mixture of Example 7 are added 0.05% of stabiliser S1-1 and 0.3% of the monomer RM-1.
• Example 7 To 99.7% of the LC mixture of Example 7 are added 0.3% of the monomer RM-35.
• Example 6 To 99.7% of the LC mixture of Example 6 are added 0.3% of the monomer RM-120.
• Example 5 To 99.699% of the LC mixture of Example 5 are added 0.3% of the monomer RM-19 and 0.001% of Irgacure 651®.

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